Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

3. Acids and Bases

Acids and Bases

Organic Chemistry

3. Acids and Bases

Acids and Bases

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2:45 minutes

Problem 42h

Textbook Question

Predict the products of the following acid–base reactions.
(h)

Verified step by step guidance

Identify the acid and base in the reaction. In this case, +NH3CH2COOH is the acid, and -OH is the base.

Recognize that the acid, +NH3CH2COOH, has two acidic protons: one on the ammonium group (+NH3) and one on the carboxylic acid group (COOH).

Understand that the hydroxide ion (-OH) will deprotonate the most acidic proton first. Typically, the carboxylic acid proton is more acidic than the ammonium proton.

Write the deprotonation reaction of the carboxylic acid group: +NH3CH2COOH + -OH → +NH3CH2COO- + H2O.

Consider the possibility of further deprotonation. The ammonium group can also be deprotonated by another hydroxide ion: +NH3CH2COO- + -OH → NH2CH2COO- + H2O.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) between reactants. In this context, the amino acid +NH3CH2COOH acts as an acid, donating protons to the base, which is the hydroxide ion (OH-). Understanding the nature of acids and bases, including their ability to donate or accept protons, is crucial for predicting the products of such reactions.

Zwitterions

A zwitterion is a molecule with both positive and negative charges, but which is overall electrically neutral. Amino acids like +NH3CH2COOH can exist as zwitterions, where the amino group is protonated (+NH3) and the carboxyl group is deprotonated (COO-). Recognizing this form is essential for understanding how amino acids behave in different pH environments, especially in acid-base reactions.

Deprotonation

Deprotonation is the removal of a proton (H+) from a molecule, resulting in the formation of a conjugate base. In the given reaction, the hydroxide ions (OH-) will deprotonate the amino acid, leading to the formation of water and the conjugate base of the amino acid. This process is key to predicting the products of the reaction, as it determines the new chemical species formed.